Exploiting the repertoire of CK2 inhibitors to target DYRK and PIM kinases

Biochimica et Biophysica Acta - Proteins and Proteomics

Volumn 1834, Issue 7, 2013, Pages 1402-1409

  Cozza, Giorgio ^a   Sarno, Stefania ^a   Ruzzene, Maria ^a   Girardi, Cristina ^a   Orzeszko, Andrzej ^b,c   Kazimierczuk, Zygmunt ^b   Zagotto, Giuseppe ^a   Bonaiuto, Emanuela ^a   Di Paolo, Maria Luisa ^a   Pinna, Lorenzo A ^a  

^a UNIVERSITY OF PADOVA   (Italy)

^b WARSAW UNIVERSITY OF LIFE SCIENCES   (Poland)

^c MILITARY UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Cancer; CK2; Dual kinase inhibitor; DYRK1A; Neurodegenerative disease; PIM1

Indexed keywords

1 ( 2' DEOXYRIBOFURANOSYL) 4,5,6,7 TETRABROMO 1H BENZIMIDAZOLE; 4,5,6,7 TETRABROMO 1H BENZIMIDAZOLE; 8 HYDROXY 4 METHYLBENXO[G]CHROMEN 2 ONE; 9H FLUORENE 2,7,9 TRIOL; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; C 624; CASEIN KINASE II; CASEIN KINASE II INHIBITOR; DRYK PROTEIN; FL 11; HARMINE; NAPHTO[ 1,2 B]BENZOFURAN 5,9 DIOL; ONCOPROTEIN; PIM KINASE; PROTEIN KINASE; PROTEIN KINASE INHIBITOR; PROTEIN KINASE PIM 1; PROTEIN SERINE THREONINE KINASE INHIBITOR; SUGAR; UNCLASSIFIED DRUG;

ADIPOCYTE; ARTICLE; CANCER CELL; CELL MEMBRANE; CELL PERMEABILIZATION; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYTOTOXICITY; DRUG EFFICACY; DRUG POTENCY; DRUG SELECTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; PRIORITY JOURNAL; PROTEIN TARGETING;

ADENOSINE TRIPHOSPHATE; ADIPOCYTES; BENZIMIDAZOLES; BINDING SITES; CASEIN KINASE II; CELLS, CULTURED; DOSE-RESPONSE RELATIONSHIP, DRUG; HARMINE; HUMANS; KINETICS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MONOAMINE OXIDASE; MONOAMINE OXIDASE INHIBITORS; PHOSPHORYLATION; PROTEIN BINDING; PROTEIN KINASE INHIBITORS; PROTEIN STRUCTURE, TERTIARY; PROTEIN-SERINE-THREONINE KINASES; PROTEIN-TYROSINE KINASES; PROTO-ONCOGENE PROTEINS C-PIM-1;

EID: 84878887568     PISSN: 15709639     EISSN: 18781454     Source Type: Journal    
DOI: 10.1016/j.bbapap.2013.01.018     Document Type: Article

References (39)

1. M. Salvi, S. Sarno, L. Cesaro, H. Nakamura, and L.A. Pinna Extraordinary pleiotropy of protein kinase CK2 revealed by weblogo phosphoproteome analysis Biochim. Biophys. Acta 1793 2009 847 859
2. M. Ruzzene, and L.A. Pinna Addiction to protein kinase CK2: a common denominator of diverse cancer cells? Biochim. Biophys. Acta 1804 2010 499 504
3. R. Zandomeni, M.C. Zandomeni, D. Shugar, and R. Weinmann Casein kinase type II is involved in the inhibition by 5,6-dichloro-1-beta-D- ribofuranosylbenzimidazole of specific RNA polymerase II transcription J. Biol. Chem. 261 1986 3414 3419 (Pubitemid 17204962)
4. R. Szyszka, N. Grankowski, K. Felczak, and D. Shugar Halogenated benzimidazoles and benzotriazoles as selective inhibitors of protein kinases CK I and CK II from Saccharomyces cerevisiae and other sources Biochem. Biophys. Res. Commun. 208 1995 418 424
5. M.A. Pagano, F. Meggio, M. Ruzzene, M. Andrzejewska, Z. Kazimierczuk, and L.A. Pinna 2-Dimethylamino-4,5,6,7-tetrabromo-1H-benzimidazole: a novel powerful and selective inhibitor of protein kinase CK2 Biochem. Biophys. Res. Commun. 321 2004 1040 1044 (Pubitemid 39044414)
6. S. Sarno, H. Reddy, F. Meggio, M. Ruzzene, S.P. Davies, A. Donella-Deana, D. Shugar, and L.A. Pinna Selectivity of 4,5,6,7-tetrabromobenzotriazole, an ATP site-directed inhibitor of protein kinase CK2 ('casein kinase-2') FEBS Lett. 496 2001 44 48 (Pubitemid 32436419)
7. M.A. Pagano, J. Bain, Z. Kazimierczuk, S. Sarno, M. Ruzzene, G. Di Maira, M. Elliott, A. Orzeszko, G. Cozza, F. Meggio, and L.A. Pinna The selectivity of inhibitors of protein kinase CK2: an update Biochem. J. 415 2008 353 365
8. R. Battistutta, G. Cozza, F. Pierre, E. Papinutto, G. Lolli, S. Sarno, S.E. O'Brien, A. Siddiqui-Jain, M. Haddach, K. Anderes, D.M. Ryckman, F. Meggio, and L.A. Pinna Unprecedented selectivity and structural determinants of a new class of protein kinase CK2 inhibitors in clinical trials for the treatment of cancer Biochemistry 50 2011 8478 8488
9. A. Siddiqui-Jain, D. Drygin, N. Streiner, P. Chua, F. Pierre, S.E. O'Brien, J. Bliesath, M. Omori, N. Huser, C. Ho, C. Proffitt, M.K. Schwaebe, D.M. Ryckman, W.G. Rice, and K. Anderes CX-4945, an orally bioavailable selective inhibitor of protein kinase CK2, inhibits prosurvival and angiogenic signaling and exhibits antitumor efficacy Cancer Res. 70 2010 10288 10298
10. J. Park, W.J. Song, and K.C. Chung Function and regulation of Dyrk1A: towards understanding Down syndrome Cell Mol. Life Sci. 66 2009 3235 3240
11. J.H. Sitz, K. Baumgartel, B. Hammerle, C. Papadopoulos, P. Hekerman, F.J. Tejedor, W. Becker, and B. Lutz The Down syndrome candidate dual-specificity tyrosine phosphorylation-regulated kinase 1A phosphorylates the neurodegeneration-related septin 4 Neuroscience 157 2008 596 605
12. J.E. Kang, S.A. Choi, J.B. Park, and K.C. Chung Regulation of the proapoptotic activity of huntingtin interacting protein 1 by Dyrk1 and caspase-3 in hippocampal neuroprogenitor cells J. Neurosci. Res. 81 2005 62 72 (Pubitemid 41139111)
13. W. Becker, and W. Sippl Activation, regulation, and inhibition of DYRK1A FEBS J. 278 2011 246 256
14. F.J. Tejedor, and B. Hammerle MNB/DYRK1A as a multiple regulator of neuronal development FEBS J. 278 2011 223 235
15. H. Kim, S.O. Sablin, and R.R. Ramsay Inhibition of monoamine oxidase A by beta-carboline derivatives Arch. Biochem. Biophys. 337 1997 137 142 (Pubitemid 27198065)
16. J. Bain, L. Plater, M. Elliott, N. Shpiro, C.J. Hastie, H. McLauchlan, I. Klevernic, J.S. Arthur, D.R. Alessi, and P. Cohen The selectivity of protein kinase inhibitors: a further update Biochem. J. 408 2007 297 315
17. R. Akue-Gedu, E. Debiton, Y. Ferandin, L. Meijer, M. Prudhomme, F. Anizon, and P. Moreau Synthesis and biological activities of aminopyrimidyl-indoles structurally related to meridianins Bioorg. Med. Chem. 17 2009 4420 4424
18. K.A. Koo, N.D. Kim, Y.S. Chon, M.S. Jung, B.J. Lee, J.H. Kim, and W.J. Song QSAR analysis of pyrazolidine-3,5-diones derivatives as Dyrk1A inhibitors Bioorg. Med. Chem. Lett. 19 2009 2324 2328
19. M. Chioua, A. Samadi, E. Soriano, O. Lozach, L. Meijer, and J. Marco-Contelles Synthesis and biological evaluation of 3,6-diamino-1H- pyrazolo[3,4-b]pyridine derivatives as protein kinase inhibitors Bioorg. Med. Chem. Lett. 19 2009 4566 4569
20. A. Beauchard, H. Laborie, H. Rouillard, O. Lozach, Y. Ferandin, R. Le Guevel, C. Guguen-Guillouzo, L. Meijer, T. Besson, and V. Thiery Synthesis and kinase inhibitory activity of novel substituted indigoids Bioorg. Med. Chem. 17 2009 6257 6263
21. R. Frederick, C. Bruyere, C. Vancraeynest, J. Reniers, C. Meinguet, L. Pochet, A. Backlund, B. Masereel, R. Kiss, and J. Wouters Novel trisubstituted harmine derivatives with original in vitro anticancer activity J. Med. Chem. 55 2012 6489 6501
22. T. Tahtouh, J.M. Elkins, P. Filippakopoulos, M. Soundararajan, G. Burgy, E. Durieu, C. Cochet, R. Schmid, D. Lo, F. Delhommel, A. Oberholzer, P. Laurence, F. Carreaux, J.P. Bazureau, S. Knapp, and L. Meijer Selectivity, co-crystal structures and neuroprotective properties of Leucettines, a family of protein kinase inhibitors derived from the marine sponge alkaloid Leucettamine B J. Med. Chem. 55 2012 9312 9330
23. M.C. Nawijn, A. Alendar, and A. Berns For better or for worse: the role of Pim oncogenes in tumorigenesis Nat. Rev. Cancer 11 2011 23 34
24. R. Amaravadi, and C.B. Thompson The survival kinases Akt and Pim as potential pharmacological targets J. Clin. Invest. 115 2005 2618 2624 (Pubitemid 41434384)
25. M. Lopez-Ramos, R. Prudent, V. Moucadel, C.F. Sautel, C. Barette, L. Lafanechere, L. Mouawad, D. Grierson, F. Schmidt, J.C. Florent, P. Filippakopoulos, A.N. Bullock, S. Knapp, J.B. Reiser, and C. Cochet New potent dual inhibitors of CK2 and Pim kinases: discovery and structural insights FASEB J. 24 2010 3171 3185
26. C.C.G. Molecular Operating Environment (MOE 2009.10), Inc, 1255 University St., Suite 1600, Montreal, Quebec, Canada, H3B 3X3.
27. G. Jones, P. Willett, R.C. Glen, A.R. Leach, and R. Taylor Development and validation of a genetic algorithm for flexible docking J. Mol. Biol. 267 1997 727 748 (Pubitemid 27170693)
28. S. Sarno, M. Mazzorana, R. Traynor, M. Ruzzene, G. Cozza, M.A. Pagano, F. Meggio, G. Zagotto, R. Battistutta, and L.A. Pinna Structural features underlying the selectivity of the kinase inhibitors NBC and dNBC: role of a nitro group that discriminates between CK2 and DYRK1A Cell Mol. Life Sci. 69 2012 449 460
29. P.P. Graczyk Gini coefficient: a new way to express selectivity of kinase inhibitors against a family of kinases J. Med. Chem. 50 2007 5773 5779 (Pubitemid 350106032)
30. E. Bonaiuto, M. Lunelli, M. Scarpa, R. Vettor, G. Milan, and M.L. Di Paolo A structure-activity study to identify novel and efficient substrates of the human semicarbazide-sensitive amine oxidase/VAP-1 enzyme Biochimie 92 2010 858 868
31. M. Zhou, and N. Panchuk-Voloshina A one-step fluorometric method for the continuous measurement of monoamine oxidase activity Anal. Biochem. 253 1997 169 174 (Pubitemid 27508168)
32. M. Ruzzene, D. Penzo, and L.A. Pinna Protein kinase CK2 inhibitor 4,5,6,7-tetrabromobenzotriazole (TBB) induces apoptosis and caspase-dependent degradation of haematopoietic lineage cell-specific protein 1 (HS1) in Jurkat cells Biochem. J. 364 2002 41 47 (Pubitemid 34538944)
33. G. Di Maira, F. Brustolon, J. Bertacchini, K. Tosoni, S. Marmiroli, L.A. Pinna, and M. Ruzzene Pharmacological inhibition of protein kinase CK2 reverts the multidrug resistance phenotype of a CEM cell line characterized by high CK2 level Oncogene 26 2007 6915 6926 (Pubitemid 47609076)
34. F. Meggio, M.A. Pagano, S. Moro, G. Zagotto, M. Ruzzene, S. Sarno, G. Cozza, J. Bain, M. Elliott, A.D. Deana, A.M. Brunati, and L.A. Pinna Inhibition of protein kinase CK2 by condensed polyphenolic derivatives. An in vitro and in vivo study Biochemistry 43 2004 12931 12936 (Pubitemid 39331813)
35. M. Bortolato, K. Chen, and J.C. Shih Monoamine oxidase inactivation: from pathophysiology to therapeutics Adv. Drug Deliv. Rev. 60 2008 1527 1533
36. M.B. Youdim, D. Edmondson, and K.F. Tipton The therapeutic potential of monoamine oxidase inhibitors Nat. Rev. Neurosci. 7 2006 295 309
37. P. Zien, O. Abramczyk, K. Domanska, M. Bretner, and R. Szyszka TBBz but not TBBt discriminates between two molecular forms of CK2 in vivo and its implications Biochem. Biophys. Res. Commun. 312 2003 623 628 (Pubitemid 37468216)
38. G. Cozza, M. Mazzorana, E. Papinutto, J. Bain, M. Elliott, G. di Maira, A. Gianoncelli, M.A. Pagano, S. Sarno, M. Ruzzene, R. Battistutta, F. Meggio, S. Moro, G. Zagotto, and L.A. Pinna Quinalizarin as a potent, selective and cell-permeable inhibitor of protein kinase CK2 Biochem. J. 421 2009 387 395
39. S. Sarno, E. Papinutto, C. Franchin, J. Bain, M. Elliott, F. Meggio, Z. Kazimierczuk, A. Orzeszko, G. Zanotti, R. Battistutta, and L.A. Pinna ATP site-directed inhibitors of protein kinase CK2: an update Curr. Top. Med. Chem. 11 2011 1340 1351